WO2020218457A1 - Composition de résine durcissable, produit durci de composition de résine durcissable, procédé de production pour composition de résine durcissable et produit durci de composition de résine durcissable, et dispositif à semi-conducteur - Google Patents
Composition de résine durcissable, produit durci de composition de résine durcissable, procédé de production pour composition de résine durcissable et produit durci de composition de résine durcissable, et dispositif à semi-conducteur Download PDFInfo
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- WO2020218457A1 WO2020218457A1 PCT/JP2020/017580 JP2020017580W WO2020218457A1 WO 2020218457 A1 WO2020218457 A1 WO 2020218457A1 JP 2020017580 W JP2020017580 W JP 2020017580W WO 2020218457 A1 WO2020218457 A1 WO 2020218457A1
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- composition
- epoxy compound
- cured resin
- compound
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- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical group C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims abstract description 18
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical compound [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0233—Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/26—Di-epoxy compounds heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/688—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/295—Organic, e.g. plastic containing a filler
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
Definitions
- the present invention relates to a composition for a cured resin for obtaining a highly heat-resistant cured product, the cured product thereof, and a composition for the cured resin and a method for producing the cured product. Further, the present invention relates to a semiconductor device using the cured product as a sealing material.
- Thermosetting resins are used in various applications such as semiconductor encapsulants and fiber reinforced plastics, and benzoxazine compounds are used as one of the raw materials.
- the benzoxazine compound refers to a compound having a benzoxazine ring containing a benzene skeleton and an oxazine skeleton, and the benzoxazine resin, which is a cured product (polymer) thereof, has excellent physical properties such as heat resistance and mechanical strength, and has many properties. It is used as a high-performance material in various fields.
- Patent Document 1 discloses an epoxy resin composition containing a benzoxazine compound having a specific structure and an epoxy compound having an aromatic ring in the main chain, and the epoxy resin provides a glass transition point (Tg) of about 200 ° C. or higher. It is described.
- the present inventors have contained (A) a polyfunctional benzoxazine compound, (B) a specific epoxy compound, and (C) a curing agent, and (A). , (B) and (C) have developed a composition for a cured resin having a specific weight average molecular weight in terms of polystyrene, and the composition for a cured resin has excellent room temperature stability, and the cured product is We have found that it has excellent heat resistance and have completed the present invention.
- a composition for a cured resin having a polystyrene-equivalent weight average molecular weight of the formulation comprising (A), (B) and (C) of 350 or more and 650 or less.
- R represents a chain alkyl group having 1 to 12 carbon atoms, a cyclic alkyl group having 3 to 8 carbon atoms, or an aryl group having 6 to 14 carbon atoms, and the aryl group is a halogen as a substituent. Alternatively, it may have a chain alkyl group having 1 to 12 carbon atoms.
- Z represents hydrogen, a hydrocarbon group having 1 to 8 carbon atoms and / or a linking group, which may be the same or different from each other, and at least one is a linking group, and the linking group causes benzo.
- the oxazine rings are linked to each other.
- L is a divalent organic group having 1 to 5 aromatic rings or an alkylene group having 2 to 10 carbon atoms, and the organic group and the alkylene group contain oxygen and / or sulfur. You may.
- [2] The composition for a cured resin according to [1], wherein the epoxy compound having at least one norbornane structure (B) and at least two epoxy groups is an alicyclic epoxy compound.
- the (B) epoxy compound is at least one selected from the group consisting of an epoxy compound having a biphenyl skeleton, a trisphenol methane type epoxy compound, a naphthalene type epoxy compound, a novolac type epoxy compound, and a phenol aralkyl type epoxy compound.
- [5] The composition for a cured resin according to any one of [1] to [4], which further contains (D) a curing accelerator.
- [6] The composition for a cured resin according to any one of [1] to [5], which further contains (E) an inorganic filler.
- [8] A semiconductor device in which a semiconductor element is installed in a cured product obtained by curing the cured resin composition according to any one of [1] to [6].
- [9] The method for producing a composition for a cured resin according to any one of [1] to [6].
- C Step of mixing with a curing agent to obtain a mixture, A method for producing a composition for a cured resin, which comprises a step of processing the mixture into a powder-like, pellet-like, or granular composition for a cured resin.
- R represents a chain alkyl group having 1 to 12 carbon atoms, a cyclic alkyl group having 3 to 8 carbon atoms, or an aryl group having 6 to 14 carbon atoms, and the aryl group is a halogen as a substituent. Alternatively, it may have a chain alkyl group having 1 to 12 carbon atoms.
- Z represents hydrogen, a hydrocarbon group having 1 to 8 carbon atoms and / or a linking group, which may be the same or different from each other, and at least one is a linking group, and the linking group causes benzo.
- the oxazine rings are linked to each other.
- L is a divalent organic group having 1 to 5 aromatic rings or an alkylene group having 2 to 10 carbon atoms, and the organic group and the alkylene group contain oxygen and / or sulfur. You may.
- L is a divalent organic group having 1 to 5 aromatic rings or an alkylene group having 2 to 10 carbon atoms, and the organic group and the alkylene group contain oxygen and / or sulfur. You may.
- [10] The production method according to [9], wherein in the step of obtaining the mixture, (D) a curing accelerator and / or (E) an inorganic filler is further mixed to obtain a mixture.
- a method for producing a cured product which comprises a step of heating the composition for a cured resin produced by the method according to [9] or [10] at 150 to 300 ° C. for 20 seconds to 5 hours to cure the composition.
- the composition for a cured resin of the present invention is a novel composition for a cured resin containing the components (A) to (C), and optionally the components (D) and (E), and the composition for a cured resin is It has the characteristics of being excellent in room temperature stability and the cured product having excellent heat resistance. Therefore, the composition for a cured resin of the present invention is used for applications in which the cured product is required to have heat resistance while being required to be stable at room temperature, for example, an adhesive, a sealing material, a paint, a matrix resin for composite materials, and the like. It can be used for various purposes.
- the composition for a cured resin of the present invention can exhibit excellent sealing performance as a semiconductor element encapsulant, and can contribute to high reliability of a semiconductor device. Further, according to the present invention, the formulation composed of the components (A) to (C) can be used as a room temperature stability / or heat resistance improving agent for the cured resin composition.
- composition for cured resin composition for cured resin
- the "compound” in the components (A), (B) and (C) of the present invention is not only the monomer represented by each formula, but also an oligomer in which the monomer is polymerized in a small amount, that is, a cured resin is formed. It shall also include the prepolymer before it is used. Therefore, the composition for a curable resin of the present invention may be a curable resin composition.
- the component (A) constituting the composition for a cured resin is at least one selected from a polyfunctional benzoxazine compound having a structural unit of the formula (1) and a polyfunctional benzoxazine compound represented by the structure of the formula (2).
- Z of the above formula (1) represents hydrogen, a substituent and / or a linking group (spacer), which may be the same or different, and at least one is a linking group.
- the benzoxazine rings are linked to each other by a linking group.
- the linking group includes a group in which two benzoxazine rings are directly bonded without interposing another group.
- the above formula (1) represents the structural unit of a compound in which two or more benzoxazine rings are linked at the benzene ring portion among the choices of the component (A).
- the polyfunctional benzoxazine compound of the formula (1) can be represented as a structure represented by the formula (1a).
- R represents a chain alkyl group having 1 to 12 carbon atoms, a cyclic alkyl group having 3 to 8 carbon atoms, or an aryl group having 6 to 14 carbon atoms, and the aryl group is a halogen as a substituent. Alternatively, it may have a chain alkyl group having 1 to 12 carbon atoms. R may be the same or different.
- X is hydrogen or a hydrocarbon group having 1 to 8 carbon atoms, and may be the same or different from each other.
- Y is an alkylene group having 1 to 6 carbon atoms, oxygen, sulfur, two SO groups, or a carbonyl group.
- m is 0 or 1.
- n is an integer from 1 to 10.
- the following groups can be exemplified as specific examples of R in the formulas (1) and (1a).
- Examples of the chain alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group and a t-butyl group.
- Examples of the cyclic alkyl group having 3 to 8 carbon atoms include a cyclopentyl group and a cyclohexyl group.
- Examples of the aryl group having 6 to 14 carbon atoms include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenanthryl group, and a biphenyl group.
- the aryl group having 6 to 14 carbon atoms may be substituted, and examples of the substituent include a chain alkyl group having 1 to 12 carbon atoms or a halogen.
- Examples of the aryl group having 6 to 14 carbon atoms substituted with a chain alkyl group having 1 to 12 carbon atoms or a halogen include an o-tolyl group, an m-tolyl group, a p-tolyl group, a xylyl group, and an o-.
- Ethylphenyl group, m-ethylphenyl group, p-ethylphenyl group, ot-butylphenyl group, mt-butylphenyl group, pt-butylphenyl group, o-chlorophenyl group, o-bromophenyl group Can be mentioned.
- R is preferably selected from a methyl group, an ethyl group, a propyl group, a phenyl group, and a p-tolyl group.
- the component (A) may be a mixture of a plurality of types of compounds represented by the formulas (1) or (1a), each having a different R.
- Examples of the hydrocarbon group having 1 to 8 carbon atoms in Z of the formula (1) and X of the formula (1a) include an alkyl group, an aryl group, an aralkyl group and the like, and an aryl group is preferable.
- Examples of the polyfunctional benzoxazine compound represented by the formula (1) or (1a) include a compound represented by the following formula (1X) and an oligomer obtained by polymerizing a small amount of the compound.
- the polyfunctional benzoxazine compound of the formula (2) which is another option of the component (A), is a compound in which nitrogen atoms (N atoms) of two benzoxazine rings are bonded to each other via a linking group L.
- L is a divalent organic group having 1 to 5 aromatic rings or an alkylene group having 2 to 10 carbon atoms, and the organic group and the alkylene group contain oxygen and / or sulfur. You may.
- the composition of the present invention may contain a plurality of types of polyfunctional benzoxazine compounds represented by the formula (2) and having different L as the component (A).
- L in the formula (2) is a group having an aromatic ring
- the number of aromatic rings is 1 to 5, and examples thereof include monocyclic compounds, polycyclic compounds, and condensed ring compounds.
- L may contain at least one selected from the group consisting of oxygen and sulfur.
- a group represented by the following formula (3) can be mentioned.
- L in the formula (3) is an alkylene group
- the number of carbon atoms thereof may be 1 to 10, preferably 1 to 6.
- Specific examples of the alkylene group include a methylene group, an ethylene group, an isopropylidene group and the like, and a methylene group is preferable.
- Examples of the polyfunctional benzoxazine compound of the formula (2) include a compound represented by the following formula (2X) and an oligomer obtained by polymerizing the compound, for example, an oligomer polymerized in a small amount.
- a commercially available product can also be used as the polyfunctional benzoxazine compound of the component (A).
- Examples of commercially available products include bisphenol F-aniline (FA) type benzoxazine and phenol-diaminodiphenylmethane (Pd) type benzoxazine (all manufactured by Shikoku Chemicals Corporation).
- the component (B) constituting the cured resin composition is an epoxy compound.
- Such epoxy compounds include at least one epoxy compound having at least one norbornane structure and at least two epoxy groups.
- the composition of the present invention may further contain an epoxy compound other than the epoxy compound having at least one norbornane structure and at least two epoxy groups as the component (B) as long as the effects of the present invention are not impaired.
- Examples of the epoxy compound other than the epoxy compound having at least one norbornan structure and at least two epoxy groups include an epoxy compound having a biphenyl skeleton, a trisphenol methane type epoxy compound, a naphthalene type epoxy compound, a novolak type epoxy compound, and a phenol aralkyl type.
- Epoxy compounds and the like can be mentioned, but an epoxy compound having a biphenyl skeleton and a trisphenol methane type epoxy compound are preferable. There may be a plurality of types of epoxy compounds other than the epoxy compound having at least one norbornane structure and at least two epoxy groups.
- Epoxy compound having at least one norbornane structure and at least two epoxy groups The epoxy compound having at least one norbornane structure and at least two epoxy groups is not particularly limited as long as it does not interfere with the effects of the present invention, but an alicyclic epoxy compound is preferable and is represented by the following formula (4). It is more preferable to have an epoxy structure bonded to a membered ring, a 6-membered ring or a norbornane ring.
- the alicyclic epoxy compound is a compound having an epoxy group which is a reactive group on the alicyclic skeleton.
- a carbon-carbon bond forming a 5-membered ring, a 6-membered ring or a norbornan ring and a carbon-carbon bond of the epoxy group are shared.
- examples thereof include an epoxy compound having the above-mentioned structure, and a compound having no glycidyl group is preferable. By using such a compound, high heat resistance can be realized. These may be used alone or in combination of 2 or more.
- the compound of the following formula (5-1) synthesizes the compound (a) having the following norbornane structure by, for example, the Diels-Alder reaction of butadiene and dicyclopentadiene, and then as shown in the following formula (6). Can be produced by reacting compound (a) with metachloroperbenzoic acid.
- the compound (b) (tricyclopentadiene) having the following norbornane structure is synthesized by the Diels-Alder reaction of cyclopentadiene and dicyclopentadiene, and then the compound of the following formula (5-2) is synthesized. As shown in (7), it can be produced by reacting compound (b) with metachloroperbenzoic acid.
- the compound (c) having the following norbornane structure is synthesized by the Diels-Alder reaction of butadiene and cyclopentadiene, and then as shown in the following formula (8). It can be produced by reacting compound (c) with metachloroperbenzoic acid.
- the compound of the following formula (5-4) can be produced, for example, by reacting dicyclopentadiene with potassium peroxymonosulfate (oxone).
- the dicyclopentadiene epoxide which is a compound of the formula (5-4), may be a commercially available product, and examples of the commercially available product include dicyclopentadiene epoxide manufactured by SHANDONG QIHUAN BIOCHEMICAL CO., LTD.
- the epoxy compound having a biphenyl skeleton is not particularly limited as long as it does not interfere with the effects of the present invention, but is preferably an epoxy compound represented by the structure of the following formula (9-1) or formula (9-2).
- an epoxy compound represented by the structure of the following formula (9-1) and an epoxy compound represented by the structure of the following formula (9-2) may be used. Seeds may be mixed and used.
- An epoxy compound having a more preferable biphenyl skeleton is an epoxy compound represented by the structure of the following formula (9-1).
- R 1 is a substituent and is an alkyl group having 1 to 4 carbon atoms, which may be the same or different.
- m is the number of the substituents R 1, is an integer of 0-4.
- n is an average value, which is 1 to 5.
- R 1 to R 8 are hydrogen atoms, halogen atoms, or alkyl groups having 1 to 4 carbon atoms, which may be the same or different.
- the m of the formula (9-1) is preferably 0 to 2, and more preferably 0.
- N in the formula (9-1) is preferably 1 to 5, and more preferably 1 to 4.
- the substituent R 1, a methyl group, an ethyl group are preferable.
- an epoxy compound having a biphenyl skeleton may each be a mixture of R 1, m, the compounds shown in n different formulas (9-1).
- Examples of the alkyl group having 1 to 4 carbon atoms in R 1 to R 8 of the formula (9-2) include a methyl group, an ethyl group, a propyl group, a butyl group and the like.
- the R 1, R 2, R 3 , R 4, R 5, R 6, R 7 or R 8,, hydrogen atom or a methyl group is preferable.
- an epoxy compound having a biphenyl skeleton may each be a mixture of R 1 ⁇ R 8 is different from the formula (9-2) to indicate compounds.
- an epoxy compound having a biphenyl skeleton used in the present invention wherein in the R 1, R 2, R 3 and R 4 carbons 1-4 (9-2) It is an alkyl group, and R 5 , R 6 , R 7 and R 8 are hydrogen atoms.
- R 1 , R 2 , R 3 and R 4 in the formula (9-2) are methyl groups.
- R 5 , R 6 , R 7 and R 8 are hydrogen atoms.
- epoxy compounds represented by the structure of formula (9-2) include YX4000 (trade name, Mitsubishi Chemical Corporation), YX4000H (trade name, Mitsubishi Chemical Corporation), YL6121H (trade name, Mitsubishi Chemical Corporation). ) Etc. can be mentioned. These may be used alone or in combination of 2 or more.
- the trisphenol methane type epoxy compound is not particularly limited as long as it does not interfere with the effects of the present invention, but is preferably an epoxy compound represented by the structure of the following formula (10).
- R is a substituent, and each independently represents an alkyl group having 1 to 6 carbon atoms, an allyl group, or a phenyl group.
- m is the number of substituents R and represents an integer of 0 to 3, respectively.
- n is an average value, and 0 ⁇ n ⁇ 10.
- the m of the formula (10) is preferably 0 to 2, and more preferably 0.
- N in the formula (10) is preferably 0 or more and 5 or less.
- Examples of the alkyl group having 1 to 6 carbon atoms in the substituent R of the formula (10) include a methyl group, an ethyl group, a propyl group, a butyl group, a cyclohexyl group and the like.
- the substituent R a methyl group is preferable.
- the trisphenol methane type epoxy compound may be a mixture of compounds represented by the formula (10) having different R, m and n, respectively.
- EPPN-501H (trade name, manufactured by Nippon Kayaku Co., Ltd.), EPPN-501HY (trade name, manufactured by Nippon Kayaku Co., Ltd.), EPPN-502H (trade name, manufactured by Nippon Kayaku Co., Ltd.).
- EPPN-503 (trade name, manufactured by Nippon Kayaku Co., Ltd.) and the like can be exemplified. These may be used alone or in combination of 2 or more.
- the naphthalene type epoxy compound is not particularly limited as long as it does not interfere with the effects of the present invention, and examples thereof include a naphthylene ether type epoxy compound, a binaphthalene type epoxy compound, and a naphthol type epoxy compound, and a naphthylene ether type epoxy compound is preferable. , Vinaphthalene type epoxy compound.
- the naphthylene ether type epoxy compound is not particularly limited as long as it does not interfere with the effects of the present invention, but is preferably an epoxy compound represented by the structure of the following formula (11).
- n is an integer of 1 or more and 20 or less
- l is an integer of 0 to 2
- R 1 is a substituent, which are independently benzyl groups, alkyl groups or formula (11a).
- the structure is represented by, and R 2 is independently a hydrogen atom or a methyl group.
- Ar is independently a phenylene group or a naphthylene group
- R 2 is independently a hydrogen atom or a methyl group
- m is an integer of 1 or 2.
- the naphthylene ether type epoxy compound may be a mixture of compounds represented by the formula (11) in which R 1 , R 2 , l and n are different from each other.
- Examples of the naphthylene ether type epoxy compound represented by the general formula (11) include those represented by the formula (11-1).
- n is an integer of 1 or more and 20 or less, preferably an integer of 1 or more and 10 or less, and more preferably an integer of 1 or more and 8 or less.
- R is a substituent.
- m is an integer of 1 or 2.
- Examples of the naphthylene ether type epoxy compound represented by the formula (11-1) include those represented by the formulas (11-2) to (11-6).
- naphthylene ether type epoxy compound Commercially available products can also be used as the naphthylene ether type epoxy compound.
- Commercially available products of naphthylene ether type epoxy compounds include HP-6000 (trade name, DIC Corporation), EXA-7310 (trade name, DIC Corporation), EXA-7311 (trade name, DIC Corporation), EXA- Examples thereof include 7311L (trade name, DIC Corporation) and EXA-7311-G3 (trade name, DIC Corporation). These may be used alone or in combination of 2 or more.
- the binaphthalene-type epoxy compound is not particularly limited as long as it does not interfere with the effects of the present invention and does not contain the above-mentioned naphthylene ether-type epoxy compound, but an epoxy compound represented by the structure of the following formula (12) is preferable.
- X represents an alkylene group having 1 to 8 carbon atoms.
- R 1 to R 4 represent any of a group represented by the following formula (12a), a hydrogen atom, a halogen atom, a phenyl group, and an alkyl group having 1 to 4 carbon atoms.
- R 1 to R 4 may be added to any ring of the naphthalene skeleton or may be added to both rings at the same time. Of R 1 to R 4 , it is necessary to include at least two groups represented by the following general formula (12a) on average, and the other Rs may be the same or different from each other. Good. ] Furthermore, binaphthalene type epoxy compounds may each be mixtures of R 1 ⁇ R 4, X compounds shown different equation (12).
- binaphthalene type epoxy compound examples include bifunctional or higher functional binaphthalene type epoxy compounds, preferably bifunctional, trifunctional or tetrafunctional binaphthalene type epoxy compounds, and more preferably bifunctional represented by the following formula (12-1). It is a vinaphthalene type epoxy compound of.
- kits for preparing the vinaphthalene type epoxy compound can also be used as the vinaphthalene type epoxy compound.
- Examples of commercially available bifunctional binaphthalene type epoxy compounds include HP-4770 (trade name, DIC Corporation) and the like.
- Examples of commercially available products of the trifunctional vinaphthalene type epoxy compound include EXA-4750 (trade name, DIC Corporation) and the like.
- Examples of commercially available products of the tetrafunctional binaphthalene type epoxy compound include HP-4710 (trade name, DIC Corporation) and HP-4700 (trade name, DIC Corporation). These may be used alone or in combination of 2 or more.
- the novolak type epoxy compound is not particularly limited as long as it does not interfere with the effects of the present invention, but a commercially available product can also be used.
- Examples of commercially available novolak type epoxy compounds include N-730A (trade name, DIC Corporation) and N-865 (trade name, DIC Corporation). These may be used alone or in combination of 2 or more.
- the phenol aralkyl type epoxy compound is not particularly limited as long as it does not interfere with the effects of the present invention, but commercially available products can also be used.
- the blending ratio of the component (A) polyfunctional benzoxazine compound and the component (B) epoxy compound is preferably 30 parts by mass or more and 180 parts by mass or less of the component (B) with respect to 100 parts by mass of the component (A), preferably 50 parts by mass. More than 130 parts by mass is more preferable. When the blending ratio of the components (A) and (B) is within the above range, more excellent heat resistance can be obtained.
- the composition of the present invention contains a plurality of types of polyfunctional benzoxazine compounds as the component (A), the total of these compounds is 100 parts by mass.
- the composition of the present invention contains a plurality of types of epoxy compounds as the component (B), the above component (B) means the total of the plurality of types of compounds.
- the norbornan structure-containing epoxy compound When the epoxy compound of the component (B) further contains an epoxy compound other than an epoxy compound having at least one norbornan structure and at least two epoxy groups (hereinafter, also referred to as a norbornan structure-containing epoxy compound), the norbornan structure-containing epoxy compound.
- the compounding ratio (mass ratio) of the epoxy compound other than the norbornan structure-containing epoxy compound is, for example, 85:15 to 15:85, which is preferable. Is 70:30 to 30:70, more preferably 60:40 to 40:60.
- the compounding ratio is within the above range, a composition for a cured resin having better room temperature stability and a cured product having more excellent heat resistance can be obtained.
- the composition of the present invention contains a plurality of types of epoxy compounds in addition to the norbornane structure-containing epoxy compound as the component (B), the above-mentioned blending amount of the epoxy compounds other than the norbornane structure-containing epoxy compound is the total of the plurality of types of compounds. Means the amount of compounding.
- the component (C) constituting the composition for a cured resin is a curing agent.
- Specific examples of the component (C) include phenol-based curing agents, aromatic amines (for example, diethyltoluenediamine, metaphenylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, metaxylenediamine, derivatives thereof, etc.).
- Aliphatic amines eg, triethylenetetramine, isophoronediamine, etc.
- imidazoles eg, imidazole, imidazole derivatives, etc.
- dicyandiamide tetramethylguanidine
- carboxylic acid anhydride eg, methylhexahydrophthalic anhydride, etc.
- Caroic acid hydrazide eg, adipic acid hydrazide, etc.
- carboxylic acid amide polypeptide
- carboxylate eg, boron trifluoride ethylamine complex, etc.
- Lewis acid complex eg, boron trifluoride ethylamine complex, etc.
- phenolic curing agent examples include monofunctional phenols, polyfunctional phenol compounds (for example, bisphenol A, bisphenol F, dihydroxynaphthalene, bisphenol sulfides (for example, bis (4-hydroxyphenyl) sulfides, etc.), and polyphenol compounds (for example, pyrogallol).
- monofunctional phenols for example, bisphenol A, bisphenol F, dihydroxynaphthalene, bisphenol sulfides (for example, bis (4-hydroxyphenyl) sulfides, etc.), and polyphenol compounds (for example, pyrogallol).
- Phenolic resin for example, novolak type phenol resin, phenol aralkyl resin having phenylene skeleton, phenol aralkyl resin having biphenyl skeleton, naphthol aralkyl resin having phenylene skeleton, trisphenol methane type phenol resin (triphenylmethane type phenol resin) , Or a phenolic resin mainly composed of a reaction product of hydroxybenzaldehyde, formaldehyde and phenol), a copolymer of a triphenylmethane type phenol compound and a novolac type phenol compound, and a dicyclopentadiene-modified phenolic resin, etc.)
- Triphenylmethane type phenol resin triphenylmethane type phenol resin
- a phenolic resin mainly composed of a reaction product of hydroxybenzaldehyde, formaldehyde and phenol a copolymer of a triphenylmethane
- the component (C) is preferably a phenol-based curing agent, more preferably a polyfunctional phenol compound, further preferably bisphenol F or a phenol resin, and further preferably bisphenol F, a novolak type phenol resin or a phenylene skeleton. It is a phenol aralkyl resin having and a phenol aralkyl resin having a biphenylene skeleton. These may be used alone or as a mixture of two or more.
- a commercially available product can also be used as the phenolic curing agent for the component (C).
- the phenolic curing agent for the component (C) for example, bisphenol F (manufactured by Honshu Chemical Industry Co., Ltd.), bis (4-hydroxyphenyl) sulfide (TDP, manufactured by Tokyo Kasei Kogyo Co., Ltd.), 2,7-dihydroxynaphthalene (manufactured by Tokyo Kasei Kogyo Co., Ltd.), pyrogallol (Tokyo).
- novolak type phenolic resin for example, ferrite TD-2106, DIC Co., Ltd .; ferrite TD-2090, DIC Co., Ltd.
- phenol aralkyl resin having a phenylene skeleton for example, MEH-7800-4S, Meiwa) Kasei Co., Ltd.
- Phenolic aralkyl resin having a biphenyl skeleton for example, MEHC-7851SS, Meiwa Kasei Co., Ltd.
- Triphenylmethane type phenol resin HE910-20, Air Water Co., Ltd .; TPM-100, Gunei (Manufactured by Chemical Industry Co., Ltd.) and the like. These may be used alone or in combination of 2 or more.
- the blending ratio of the component (A) polyfunctional benzoxazine compound, the component (B) epoxy compound, and the total of the component (C) curing agent is 100 parts by mass of the component (A), and the components (B) and (C). ) Is preferably 40 parts by mass or more and 200 parts by mass or less, and more preferably 60 parts by mass or more and 150 parts by mass or less.
- a composition for a cured resin having better room temperature stability and a cured product having better heat resistance can be obtained. Obtainable.
- composition of the present invention contains a plurality of types of polyfunctional benzoxazine compounds as the component (A), the total of these compounds is regarded as 100 parts by mass.
- the composition of the present invention contains a plurality of types of epoxy compounds as the component (B)
- the above-mentioned “blending ratio of the component (B)” means the total ratio of the plurality of types of compounds.
- the composition of the present invention contains a plurality of types of curing agents as the component (C)
- the above-mentioned “blending ratio of the component (C)” means the total ratio of the plurality of types of curing agents.
- the polystyrene-equivalent weight average molecular weight of the formulation comprising (A), (B) and (C) is 350 or more and 650 or less, preferably 350 or more and 600 or less or 400 or more and 650 or less, and more preferably 350 or less. More than 550 or less or 450 or more and 600 or less.
- the weight average molecular weight is 350 or more and 650 or less, it is considered that the composition for a cured resin is less sticky at room temperature and is easier to handle. Therefore, when the weight average molecular weight is 350 or more and 650 or less, a composition for a cured resin having better room temperature stability can be obtained.
- the polystyrene-equivalent weight average molecular weight of the formulation comprising (A), (B) and (C) can be obtained by measuring by gel permeation chromatography (GPC) and converting to standard polystyrene.
- GPC gel permeation chromatography
- Such measurement and conversion can be easily performed by using a commercially available GPC apparatus (for example, manufactured by Tosoh Corporation) and a column (for example, TSKgel superHZ2000 (manufactured by Tosoh Corporation) and TSKgel superHZ1000 (manufactured by Tosoh Corporation)). be able to.
- the measurement and conversion can be performed under the following conditions, for example.
- (A), (B) and (C) are placed under atmospheric pressure on a hot plate whose surface temperature is set to 100 ° C. After kneading for 5 minutes with, the mixture is cooled to room temperature to obtain a mixture, which is then pulverized into a powder in a mortar, and the obtained formulation can be used.
- composition for a cured resin of the present invention may further contain (D) a curing accelerator, if desired.
- a curing accelerator a known curing accelerator can be used, and amine compounds such as tributylamine, 1,8-diazabicyclo (5,4,0) undecene-7, 2-methylimidazole, and 2-ethyl can be used.
- Imidazole compounds such as imidazole and 1,2-dimethylimidazole
- organophosphorus compounds such as triphenylphosphine in which phosphorus is bound only by covalent bonds
- tetraphenylphosphonium tetraphenylborate bis (tetrabutylphosphonium) (BTBP)- Phyllomellitic acid
- BTBP-3PC bis (tetrabutylphosphonium)
- TBP-3PC bis [(2-hydroxy-5-methylphenyl) methyl] -4-methylphenolate
- the above-mentioned curing accelerator may be used alone or in combination of two or more.
- organophosphorus compounds such as triphenylphosphine, tetraphenylphosphonium tetraphenylborate, BTBP-pyromellitic acid, and TBP-3PC are preferable because they have a greater effect of improving the curing rate.
- the organic phosphorus compound preferably exhibits a function of promoting a cross-linking reaction between an epoxy group and a phenolic hydroxyl group.
- the organic phosphorus compound also exhibits a function of accelerating the reaction between the hydroxyl group and the epoxy group generated when the polyfunctional benzoxazine compound (A) undergoes a cleavage reaction at a high temperature.
- the mixing ratio of the component (D) is such that the component (D) is in the range of 0.01 part by mass or more and 10 parts by mass or less with respect to a total of 100 parts by mass of the components (A), (B) and (C). It is preferably in the range of 0.1 parts by mass or more and 5 parts by mass or less. By containing the component (D) in this range, a composition for a cured resin having more excellent quick-curing property can be obtained.
- the composition for a cured resin of the present invention may further contain the (E) inorganic filler, if desired.
- the composition for a cured resin of the present invention when used as a sealing material for a semiconductor element or the like, it preferably contains the component (E).
- the inorganic filler used in the present invention is not particularly limited, and can be selected in consideration of the use of the cured resin composition or the cured product thereof or the properties to be imparted. Hereinafter, this inorganic filler is referred to as a component (E).
- component (E) examples include oxides such as silica, alumina, titanium oxide, zirconium oxide, magnesium oxide, cerium oxide, yttrium oxide, calcium oxide, antimony trioxide, and zinc oxide; calcium carbonate, magnesium carbonate, barium carbonate.
- Carbonates such as strontium carbonate; Sulfates such as barium sulfate, aluminum sulfate, calcium sulfate; nitrides such as aluminum nitride, silicon nitride, titanium nitride, boron nitride, manganese nitride; calcium silicate, magnesium silicate, silicic acid Silicon compounds such as aluminum; boron compounds such as aluminum borate; zirconium compounds such as barium zirconate and calcium zirconate; phosphorus compounds such as zirconium phosphate and magnesium phosphate; strontium titanate, calcium titanate, magnesium titanate, Titanium compounds such as bismuth titanate, barium titanate, potassium titanate; mica, talc, kaolin, kaolin clay, kaolinite, halloysite, cordierite, pyrophyllite, montmorillonite, sericite, amesite, bentonite, asbestos Minerals such as wollastonite, sep
- the component (E) is preferably silica, alumina and a magnetic material.
- silica include fused silica, spherical silica, crystalline silica, amorphous silica, synthetic silica, hollow silica and the like, and spherical silica and crystalline silica are preferable.
- alumina are spherical alumina, crushed alumina, microspherical alumina, preferably spherical alumina and microspherical alumina.
- Preferred magnetic materials include soft magnetic ferrite, iron oxide, chromium oxide, cobalt, non-metal oxide magnetic material (oxide) and the like.
- the component (E) may be used alone or in combination of two or more.
- the component (E) may be granular, and the average particle size in that case is not particularly limited, but examples thereof include 0.01 ⁇ m and 150 ⁇ m, preferably 0.1 ⁇ m and 120 ⁇ m, and more preferably. , 0.5 ⁇ m or more and 75 ⁇ m or less. Within this range, for example, when the composition of the present invention is used as a sealing material for semiconductor elements, the filling property into the mold cavity becomes better.
- the average particle size of the component (E) can be measured by a laser diffraction / scattering method. Specifically, it can be measured by creating a particle size distribution of the inorganic filler on a volume basis with a laser diffraction type particle size distribution measuring device and using the median diameter as the average particle size.
- the measurement sample one in which the inorganic filler is dispersed in water by ultrasonic waves can be preferably used.
- the laser diffraction type particle size distribution measuring device "LA-500”, “LA-750”, “LA-950”, “LA-960”, etc. manufactured by HORIBA, Ltd. can be used.
- the blending ratio of the component (E) is not particularly limited as long as a cured product having high heat resistance can be obtained, and can be appropriately set according to the intended use.
- the compounding ratio shown below is preferable.
- the lower limit of the blending ratio of the component (E) is, for example, 150 parts by mass or more, preferably 400 parts by mass or more, preferably 500 parts by mass, based on 100 parts by mass of the total of the components (A), (B) and (C). More than parts by mass is more preferable.
- the upper limit of the blending ratio of the component (E) is 1300 parts by mass or less, preferably 1150 parts by mass or less, and more preferably 950 parts by mass or less.
- the lower limit of the blending ratio of the component (E) is 400 parts by mass or more, the increase in the amount of moisture absorbed and the decrease in the strength due to the curing of the cured resin composition can be further suppressed, and therefore better solder crack resistance can be obtained. A cured product having can be obtained. Further, when the upper limit of the blending ratio of the component (E) is 1300 parts by mass or less, the fluidity of the composition for cured resin becomes better, it is easy to fill the mold, and the cured product is better sealed. Demonstrates stopping performance.
- the composition of the present invention may contain a benzoxazine compound other than the component (A) as long as the effects of the present invention are not impaired.
- a monofunctional benzoxazine compound having one benzoxazine ring may be added to the composition.
- composition for a cured resin of the present invention may contain, for example, nanocarbon, a flame retardant, a mold release agent, a colorant, a low stress additive, a metal hydroxide, etc. within a range that does not impair its performance. Can be done.
- nanocarbons include carbon nanotubes, fullerenes, and derivatives thereof.
- the flame retardant examples include phosphoric acid esters such as red phosphorus, triphenyl phosphate, tricresyl phosphate, trixilenyl phosphate, cresil diphenyl phosphate, xylenyl diphenyl phosphate, resorcinol bisphenyl phosphate and bisphenol A bisdiphenyl phosphate. , Borate ester, phosphazene and the like.
- the release agent include natural waxes such as stearic acid ester and carnauba wax, synthetic waxes such as polyethylene oxide wax, higher fatty acids such as stearic acid or esters thereof, metal salts such as zinc stearate, paraffin, and silicone oil. And so on.
- Examples of the colorant include carbon black, red iron oxide, titanium oxide and the like.
- Examples of the low stress additive include silicone oil and silicone rubber.
- Examples of the metal hydroxide include hydroxides such as calcium hydroxide, aluminum hydroxide, and magnesium hydroxide.
- the mixing ratio of the other components may be in the range of 0.01 parts by mass or more and 10 parts by mass or less with respect to 100 parts by mass in total of the components (A), (B) and (C). It is preferably in the range of 0.1 parts by mass or more and 9 parts by mass or less.
- the room temperature stability of the cured resin composition of the present invention can be evaluated by the glass transition temperature (also referred to as powder Tg), stickiness, and / or caking property of the cured resin composition before curing.
- the glass transition temperature of the cured resin composition is 3 ° C. or higher, preferably 5 ° C. or higher, and more preferably 6 ° C. or higher.
- the glass transition temperature can be measured by differential scanning calorimetry (DSC). Such measurement can be easily performed by using a commercially available differential scanning calorimeter (for example, manufactured by Hitachi High-Tech Science Corporation).
- the composition for a cured resin of the present invention is preferably non-sticky. Regarding the stickiness of the composition for cured resin, it can be confirmed whether or not the composition for cured resin has stickiness by the confirmation test shown below. Confirmation test: The composition for cured resin before curing is collected in a bottle, covered and sealed, and then stored in a thermostatic chamber adjusted to a temperature of 23 ⁇ 1 ° C and a humidity of 50 ⁇ 5 ° C for 24 hours. Then, 5 minutes after the bottle is turned upside down and allowed to stand, it can be determined whether or not the composition is attached to the bottom of the bottle. Further details of the above confirmation test can be carried out according to the description of Example 1 described later.
- the composition for a cured resin of the present invention contains the component (E), it is preferable that the composition for a cured resin does not solidify, or even if it solidifies, it can be loosened by turning the bottle upside down.
- the confirmation test it can be confirmed whether or not the cured resin composition is solidified by the confirmation test shown below. Confirmation test: The composition for cured resin before curing is collected in a bottle, covered and sealed, and then stored in a thermostatic chamber adjusted to a temperature of 23 ⁇ 1 ° C and a humidity of 50 ⁇ 5 ° C for 24 hours. Then, the bottle is turned upside down, and 5 minutes after allowing it to stand, the composition is visually inspected to determine the presence or absence of consolidation. Further details of the above confirmation test can be carried out according to the description of Example 15 described later.
- composition for a cured resin of the present invention a method for producing the composition for a cured resin of the present invention will be described.
- the composition for a cured resin of the present invention can be produced by performing a step of processing the mixture into a powder-like, pellet-like, or granular composition for a cured resin.
- the kneading or mixing method is not particularly limited, and for example, mixing can be performed using a mixing device such as a planetary mixer, a twin-screw extruder, a heat roll or a kneader, or a kneader.
- a mixing device such as a planetary mixer, a twin-screw extruder, a heat roll or a kneader, or a kneader.
- the components (A), (B), and (C) are in a highly viscous liquid or solid state at room temperature, or if the components (E) are contained, they are heated and kneaded as necessary. Alternatively, it may be kneaded under pressurized or reduced pressure conditions.
- the heating temperature is preferably 80 to 120 ° C.
- the composition for a cured resin containing the component (E) is in a solid state at room temperature, it may be cooled and pulverized after heating and kneading to form a powder, and the powder is tableted into pellets. May be good. Further, the powder may be granulated into granules.
- the cured resin composition of the present invention does not contain the component (E) and is used for FRP prepreg applications
- the cured resin composition preferably has a viscosity of 10 to 3000 Pa ⁇ s at 50 ° C. .. It is more preferably 10 to 2500 Pa ⁇ s, and even more preferably 100 to 2000 Pa ⁇ s.
- the viscosity is not particularly limited as long as it does not interfere with the operations such as sealing and coating.
- the cured product of the composition for a cured resin of the present invention has a feature that the glass transition temperature is high and the heat resistance is excellent.
- the reason why the composition for a cured resin of the present invention forms such an excellent cured product is considered as follows. First, in the homopolymerization of benzoxazine, phenolic hydroxyl groups are generated by the polymerization. It is considered that this phenolic hydroxyl group has low heat resistance and a low glass transition temperature because the polymer chain is cleaved by the ketoenol tautomer at a high temperature, for example, 200 ° C. or higher. Has been done.
- the polyfunctional epoxy compound having the norbornan structure of the present invention and having two or more epoxy groups is difficult to polymerize independently, and by reacting with the phenolic hydroxyl group derived from benzoxazine, the polymer chain is cleaved. Is thought to prevent. Therefore, it is considered that a cured product having high heat resistance can be obtained.
- the heat resistance of the cured product of the present invention can be evaluated by measuring the glass transition temperature of the cured product.
- the glass transition temperature of the cured product is 220 ° C. or higher, preferably 225 ° C. or higher, and more preferably 230 ° C. or higher.
- the glass transition temperature of the cured product is 230 ° C. or higher, preferably 235 ° C. or higher, and more preferably 240 ° C. or higher.
- the glass transition temperature can be measured by differential scanning calorimetry (DSC). Such measurement can be easily performed by using a commercially available differential scanning calorimeter (for example, manufactured by Hitachi High-Tech Science Corporation).
- the cured product of the present invention can be produced by performing ring-opening polymerization and curing under the same curing conditions as known benzoxazine compounds and / or epoxy compounds. For example, the following methods can be mentioned.
- the composition for a cured resin of the present invention is produced by the above method.
- the obtained cured resin composition can be heated at, for example, 150 to 300 ° C. for a curing time of, for example, 20 seconds to 5 hours, preferably 20 seconds to 1 hour to obtain a cured product. ..
- a curing time of 1 to 3 minutes is sufficient, but it is preferable to heat for another 5 minutes to 5 hours as post-curing in order to obtain higher strength.
- a solvent may be further added to obtain a composition having a solution viscosity suitable for forming a thin film.
- the solvent is not particularly limited as long as it can dissolve the components (A) to (D), and examples thereof include hydrocarbons, ethers, esters, halogen-containing compounds and the like.
- the solution-like composition for a cured resin dissolved in a solvent as described above, the solution-like composition for a cured resin is applied to a substrate or the like, the solvent is volatilized, and then heat curing is performed. A cured product can be obtained.
- the semiconductor device of the present invention is a cured product obtained by curing the composition for a cured resin of the present invention containing the components (A) to (C), optionally the component (D), the component (E), and other components. It is a semiconductor device in which a semiconductor element is installed.
- the semiconductor element is usually supported and fixed by a lead frame which is a thin plate of a metal material.
- the semiconductor element is installed in the cured product means that the semiconductor element is sealed with the cured product of the cured resin composition, and the semiconductor element is coated with the cured product. Represents a state. In this case, the entire semiconductor element may be covered, or the surface of the semiconductor element installed on the substrate may be covered.
- a sealing step is performed by a conventional molding method such as a transfer mold, a compression mold, or an injection mold.
- (B) Epoxy compound> The following (B1) to (B5) were used as the component (B).
- (B1) Epoxy compound 1 (alicyclic epoxy compound); compound of formula (5-1)
- the compound (a) represented by the above formula (6) was described as "Diels-Diels of butadiene and cyclopentadiene by Shoichi Tsuchida et al. Alder reaction-determination of trimer- ", Journal of the Petroleum Society, 1972, Vol. 15, No. 3, p189-192" was synthesized according to the method described. Next, the reaction of the above formula (6) was carried out as follows.
- Epoxy compound 2 (epoxy compound having a biphenyl skeleton): An epoxy compound having a biphenyl skeleton represented by the following formula (9-1-1) (NC-3000-H, manufactured by Nippon Kayaku Co., Ltd.) (In equation (9-1-1), n is an average value, which is 3.9.)
- Epoxy compound 3 (trisphenol methane type epoxy compound): Epoxy compound represented by the following formula (10-1) (EPPN-502H, manufactured by Nippon Kayaku Co., Ltd.) (In equation (10-1), n is an average value, which is 1.9.)
- the organic layer was washed with 100 L of a mixed aqueous solution of salt and sodium thiosulfate (salt 20 wt% + sodium thiosulfate 20 wt%), and then further washed twice with 100 L of ion-exchanged water.
- the washed organic layer was dried over magnesium sulfate, magnesium sulfate was removed by filtration, and the organic solvent was distilled off from the filtrate to obtain 11 kg of the compound represented by the following formula (5-4) as a white solid.
- Hardener 2 Hardener represented by the following formula (13-2) (MEHC-7851SS, manufactured by Meiwa Kasei Co., Ltd.) (In equation (13-2), n is an average value, which is 2.0.)
- (C3) Hardener 3 Hardener represented by the following formula (13-3) (MEH-7800-4S, manufactured by Meiwa Kasei Co., Ltd.) (In equation (13-3), n is an average value, which is 4.8.)
- Hardener 4 Hardener represented by the following formula (13-4) (TD-2106, manufactured by DIC Corporation) (In equation (13-4), n is an average value, which is 8.7.)
- (D) Curing accelerator> The following (D1) to (D4) were used as the component (D).
- TPP-K TM Tetraphenylphosphonium tetraphenylborate
- (D3) Curing accelerator 3 Bis (tetrabutylphosphonium) (BTBP) -pyromellitic acid (manufactured by Hokuko Chemical Industry Co., Ltd.) represented by the following formula.
- composition for cured resin (hereinafter, also referred to as "composition” or “composition for cured resin before curing") and the cured product are prepared as follows, and the weight average molecular weight and heat resistance of the composition for cured resin are prepared as follows.
- (A), (B1), and (C2) are kneaded under atmospheric pressure for 5 minutes on a hot plate whose surface temperature is set to 100 ° C. at the blending ratios shown in Table 1, and then cooled to room temperature. Obtained a mixture.
- the mixture was pulverized in a mortar to obtain a composition.
- ⁇ Glass transition temperature Tg> About 10 mg of the composition was weighed on an aluminum pan used in DSC and heated in an oven at 220 ° C. for 5 hours to obtain a cured product.
- the Tg of the obtained cured product was measured by DSC under the following conditions. The results are shown in Table 1.
- Examples 2 to 14, 26, 27 The composition of each example was prepared in the same manner as in Example 1 except that the blending ratio of each component was as shown in Table 1.
- the weight average molecular weight, heat resistance (glass transition temperature), and room temperature stability (powder Tg, stickiness) of each composition were measured in the same manner as in Example 1.
- the formulations in Examples 4 to 6 consist of the components (A), (B), and (C), and do not contain the component (D). The results are shown in Table 1.
- Comparative Examples 1 to 8 The compositions of each Comparative Example were prepared in the same manner as in Example 1 except that the blending ratio of each component was as shown in Table 2. The weight average molecular weight, heat resistance (glass transition temperature), and room temperature stability (powder Tg, stickiness) of each composition were measured in the same manner as in Example 1.
- the formulation in Comparative Example 2 comprises the components (A), (B), and (C), and does not contain the component (D). The results are shown in Table 2.
- the Tg of the cured product of the cured resin composition of each example is 220 ° C. or higher, indicating that it has high heat resistance. Further, since the powder Tg of the cured resin composition before curing in each example is 3 ° C. or higher and there is no stickiness, it can be seen that the room temperature stability is excellent.
- the cured resin compositions of Examples 7 to 14 were not sticky even when stored in a thermostatic chamber for 24 hours, and when turned upside down, the entire amount fell toward the lid while maintaining the shape of the bottom of the bottle. Therefore, it is considered that the cured resin compositions of Examples 7 to 14 are less sticky than the cured resin compositions of Examples 1 to 6, 26 and 27.
- the cured product obtained by curing the cured resin compositions of Comparative Examples 4 to 8 has a low Tg and is inferior in heat resistance. Further, since the powder Tg of the cured resin composition of Comparative Examples 1 to 3 before curing is less than 3 ° C. and has stickiness, it can be seen that the room temperature stability is inferior. From the above results, it can be seen that the composition for a cured resin according to the embodiment of the present invention is excellent in room temperature stability, but the cured product achieves high heat resistance.
- composition for cured resin (hereinafter, also referred to as “composition” or “composition for cured resin before curing") and the cured product are prepared as follows, and the weight average molecular weight and heat resistance of the composition for cured resin are prepared as follows.
- ⁇ Glass transition temperature; Tg> Using a transfer molding machine, the prepared composition is cured under the conditions of a mold temperature of 200 ° C., an injection pressure of 4 MPa, and a curing time of 3 minutes, and further, as a post-curing treatment, it is heated in an oven at 220 ° C. for 4 hours. A cured product having a size of 3 mm, a width of 3 mm, and a length of 15 mm was prepared. Tg was measured by DSC under the following conditions using a test piece obtained by cutting the cured product into a size of 3 mm in length ⁇ 3 mm in width ⁇ 2 mm in length. The results are shown in Table 3. Equipment: X-DSC-7000 (manufactured by Hitachi High-Tech Science Corporation) Measurement conditions: N 2 flow rate; 20 mL / min, heating rate; 20 ° C / min
- Example 15 A formulation consisting of the components (A), (B) and (C) of the composition of Example 15 was produced, and the weight average molecular weight of such a formulation was determined by GPC in the same manner as in Example 1 in terms of standard polystyrene. It was measured. Specifically, (A), (B1), and (C2) are kneaded at the blending ratios shown in Table 3 on a hot plate whose surface temperature is set to 100 ° C. under atmospheric pressure for 5 minutes. , Cooled to room temperature to give a mixture. The mixture was pulverized in a mortar to obtain a formulation. The weight average molecular weight of the obtained formulation was measured by GPC. The results are shown in Table 3.
- Example 16 to 25 The composition of each example was prepared in the same manner as in Example 15 except that the blending ratio of each component was as shown in Table 3. For each composition, the weight average molecular weight, heat resistance evaluation (glass transition temperature), and room temperature stability (consolidation) were measured in the same manner as in Example 15. The results are shown in Table 3.
- the Tg of the cured product of the cured resin composition of each example is 230 ° C. or higher, indicating that it has high heat resistance. Further, since the solidification property of the cured resin composition of the examples before curing is “ ⁇ ”, it can be seen that the composition is excellent in room temperature stability. Among them, in Examples 24 and 25, no particular consolidation of the composition was observed. On the other hand, the cured product obtained by curing the cured resin compositions of Comparative Examples 10 to 12 has a low Tg and is inferior in heat resistance. Further, since the solidification property of the cured resin composition of Comparative Example 9 before curing is “x”, it can be seen that the stability at room temperature is inferior. From the above results, it can be seen that the composition for a cured resin according to the embodiment of the present invention is excellent in room temperature stability, but the cured product achieves high heat resistance.
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Abstract
La présente invention vise à fournir une composition de résine durcissable qui a une excellente stabilité à température ambiante et est destinée à produire un produit durci qui est hautement résistant à la chaleur, etc. ; un produit durci de la composition de résine durcissable ; un procédé de production de la composition de résine durcissable et du produit durci ; et un dispositif à semi-conducteur qui utilise le produit durci en tant que matériau d'étanchéité. L'invention concerne par conséquent une composition de résine durcissable qui contient (A) un composé de benzoxazine polyfonctionnel qui a au moins deux cycles benzoxazine, (B) un composé époxy qui comprend au moins un type de composé époxy qui a au moins une structure norbornane et au moins deux groupes époxy, et (C) un agent de durcissement, le poids moléculaire moyen en poids équivalent au polystyrène d'un mélange de (A), (B), et (C) étant de 350 à 650. L'invention concerne aussi un produit durci de la composition de résine durcissable. L'invention concerne également un procédé de production de la composition de résine durcissable et du produit durci. L'invention concerne en outre dispositif à semi-conducteur dans lequel un élément à semi-conducteur est disposé dans un produit durci qui est formé par durcissement d'une composition de résine durcissable qui contient les composants (A) à (C) et, facultativement, (D) et (E).
Priority Applications (4)
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US17/606,681 US20220195188A1 (en) | 2019-04-26 | 2020-04-23 | Composition for curable resins, cured product of said composition, production method for said composition and said cured product, and semiconductor device |
CN202080030737.1A CN113728032A (zh) | 2019-04-26 | 2020-04-23 | 固化树脂用组合物、该组合物的固化物、该组合物及该固化物的制造方法、以及半导体装置 |
JP2021516225A JPWO2020218457A1 (fr) | 2019-04-26 | 2020-04-23 | |
KR1020217035463A KR20220004990A (ko) | 2019-04-26 | 2020-04-23 | 경화 수지용 조성물, 상기 조성물의 경화물, 상기 조성물 및 상기 경화물의 제조방법, 및 반도체 장치 |
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PCT/JP2020/017580 WO2020218457A1 (fr) | 2019-04-26 | 2020-04-23 | Composition de résine durcissable, produit durci de composition de résine durcissable, procédé de production pour composition de résine durcissable et produit durci de composition de résine durcissable, et dispositif à semi-conducteur |
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US (1) | US20220195188A1 (fr) |
JP (1) | JPWO2020218457A1 (fr) |
KR (1) | KR20220004990A (fr) |
CN (1) | CN113728032A (fr) |
TW (1) | TW202100707A (fr) |
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Cited By (1)
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WO2022168815A1 (fr) * | 2021-02-02 | 2022-08-11 | Eneos株式会社 | Composition pour résines durcissables, produit durci de ladite composition, procédé de production de ladite composition, procédé de production dudit produit durci, et dispositif à semi-conducteur |
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CN115703873B (zh) * | 2021-08-04 | 2023-08-01 | 华东理工大学 | 一种连续化制备主链型苯并噁嗪类衍生物的方法 |
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WO2015002071A1 (fr) * | 2013-07-04 | 2015-01-08 | 味の素株式会社 | Composition de résine photosensible |
JP2017020011A (ja) * | 2016-07-06 | 2017-01-26 | 台光電子材料(昆山)有限公司Elite Electronic Material (Kunshan) Co. Ltd | 樹脂組成物ならびにそれを使用した銅張積層板およびプリント回路板 |
WO2017188448A1 (fr) * | 2016-04-28 | 2017-11-02 | Jxtgエネルギー株式会社 | Composition pour une résine durcissable et produit durci correspondant |
US20170327683A1 (en) * | 2016-05-12 | 2017-11-16 | Elite Electronic Material (Zhongzhan) Co., Ltd. | Resin composition and product made therefrom |
WO2018105743A1 (fr) * | 2016-12-09 | 2018-06-14 | Jxtgエネルギー株式会社 | Composition de résine de durcissement, produit durci de, et procédé de durcissement destiné à, la composition de résine de durcissement, et dispositif semi-conducteur |
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JP5627196B2 (ja) | 2009-04-28 | 2014-11-19 | 国立大学法人横浜国立大学 | エポキシ樹脂組成物及びその硬化物 |
KR102544837B1 (ko) * | 2017-03-31 | 2023-06-19 | 에네오스 가부시키가이샤 | 경화 수지용 조성물, 그 조성물의 경화물, 그 조성물 및 그 경화물의 제조 방법, 및 반도체 장치 |
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- 2020-04-23 KR KR1020217035463A patent/KR20220004990A/ko unknown
- 2020-04-23 CN CN202080030737.1A patent/CN113728032A/zh active Pending
- 2020-04-23 US US17/606,681 patent/US20220195188A1/en active Pending
- 2020-04-23 WO PCT/JP2020/017580 patent/WO2020218457A1/fr active Application Filing
- 2020-04-23 JP JP2021516225A patent/JPWO2020218457A1/ja active Pending
- 2020-04-24 TW TW109113875A patent/TW202100707A/zh unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015002071A1 (fr) * | 2013-07-04 | 2015-01-08 | 味の素株式会社 | Composition de résine photosensible |
WO2017188448A1 (fr) * | 2016-04-28 | 2017-11-02 | Jxtgエネルギー株式会社 | Composition pour une résine durcissable et produit durci correspondant |
US20170327683A1 (en) * | 2016-05-12 | 2017-11-16 | Elite Electronic Material (Zhongzhan) Co., Ltd. | Resin composition and product made therefrom |
JP2017020011A (ja) * | 2016-07-06 | 2017-01-26 | 台光電子材料(昆山)有限公司Elite Electronic Material (Kunshan) Co. Ltd | 樹脂組成物ならびにそれを使用した銅張積層板およびプリント回路板 |
WO2018105743A1 (fr) * | 2016-12-09 | 2018-06-14 | Jxtgエネルギー株式会社 | Composition de résine de durcissement, produit durci de, et procédé de durcissement destiné à, la composition de résine de durcissement, et dispositif semi-conducteur |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2022168815A1 (fr) * | 2021-02-02 | 2022-08-11 | Eneos株式会社 | Composition pour résines durcissables, produit durci de ladite composition, procédé de production de ladite composition, procédé de production dudit produit durci, et dispositif à semi-conducteur |
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JPWO2020218457A1 (fr) | 2020-10-29 |
KR20220004990A (ko) | 2022-01-12 |
TW202100707A (zh) | 2021-01-01 |
US20220195188A1 (en) | 2022-06-23 |
CN113728032A (zh) | 2021-11-30 |
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